RELEASE DATE: Friday, Nov 07, 2025

DIRECTOR: Donald Petrie

CAST: Kathryn Hahn, Matthew McConaughey, Kate Hudson, Adam Goldberg, Bebe Neuwirth, Michael Michele, Shalom Harlow, Annie Parisse

Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days. Andie Anderson covers the "How To" beat for "Composure" magazine and is assigned to write an article on "How to Lose a Guy in 10 days." They meet in a bar shortly after the bet is made.